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Angiogenesis is very important in the progression of various pathological disorders, most importantly tumor growth and metastasis. This research aims to investigate the efficacy of the synthetic chalcone derivative)2-Hydroxychalcone)and its mixture with ethanolic extract of Phoenix dactylifera seeds as anti-angiogenic agents. The synthetic chalcone derivative was synthesized according to Claisen-Schmidt condensation method using SOCl2/ETOH as a catalyst with a good yield. The structure of the synthesizedchalcone derivative has been characterized by TLC, melting point, UV, and IR Spectroscopy , and elemental microanalysis (CHNO). The powdered seeds of P. dactylifera were extracted by soxhlet extraction with Ethanol. The synthetic chalcone derivative alone at concentration (17.15μg/ml) and its mixture with ethanolicextract of P. dactylifera seeds were evaluated for its anti-angiogenic activity using the ex-vivo rat aorta ring model at concentrations 17.15μg/ml and 30.9μg/ml respectively. At the previously mentioned concentrations, The synthetic chalcone derivativewas able to inhibit growth of blood vessels significantly (56.23%) in rat aorta ring assay in comparison with the negative control (P<0.05), while the mixture of the synthetic chalcone derivative and ethanolic extract of P. dactylifera seeds showed higher percentage of inhibition (76.63%)than that of the synthetic chalcone derivative alone in comparison with the negative control (P<0.05).Thisproduced effect could be due to the synergism between the synthetic chalcone derivative and the phytochemical constituents present in ethanolic extract in inhibiting different angiogenesis signaling pathways.